#19) Sex, and the "Straight Gender" Thing
Now that we’ve made it through the series about heartbreak, it’s time for some fun! We’re going to take a break from tough topics and enjoy some lighter stories to give our collective hearts a rest! For the next two stories, we’re going back to a time before I met Tara, when my life was too busy for a real relationship, and so dating was more about fun flings and learning through experiences.
This week’s story explores being a woman’s first. In recent years, even for Generation X, as LGBTQ has become more in vogue, lesbian sex has become a subject of increasing fascination. Book sales for LGBTQ-themed books have skyrocketed: up 740% in the past five years alone! Television series from “The Morning Show” to “Last Tango in Halifax” feature plotlines of Generation X women exploring relationships with women. In the dating world, I have encountered more and more women, newly single after divorcing men, who are exploring intimacy with women. Women deciding they want to try it out, and with the laissez-faire attitude of trying on different pairs of shoes at Nordstrom. We will be exploring this phenomenon in future stories.
Back in 2010, when the next two stories are set, this experimentation by newly single women was starting to pick up steam. Shows like “The L Word” for the first time brought the lives of lesbians and bisexual women into the mainstream. I was still relatively new to dating women, and the mores of meeting online. I tried to learn what worked, and how to do things differently next time. Sometimes that meant overcorrecting or overcompensating for mistakes. In the next two stories, you’ll follow my voyage from dating ultra-femme Molly, to the British banker, who was more masculine or butch.
Molly was a tall, buxom, blond, ultra-feminine, Jewish real estate agent from Connecticut. We met on a dating app, where her profile listed she was seeking men. When she wrote to me online, I asked, Are you looking for women here too? She responded, Perhaps…regardless of what profile says. This was probably the point where I should have thanked her for her interest, and kept clicking to the next profiles, but alas!
We messaged back and forth a bit. Molly was my age and a new mother, having decided, with the clock of time ticking, to have a baby alone. She had recently moved back to Connecticut, near where she grew up, so her mother could help out now and then with childcare. She was establishing her career, furnishing her new home, and caring for a newborn—not exactly a recipe for being available for a relationship.
I can see you all shaking your heads—here we go again. Amy has stumbled on yet another unavailable straight woman to date! I am also questioning why I kept making this mistake. It’s typical in the world of dating for people of all sexual orientations to seek out commonalities, be it religion, background, education, and so on. Was I unconsciously choosing women whose journeys would be similar to my own, as opposed to looking for women who would be a good fit?
For our first date, Molly offered to drive down to Westchester for dinner, saying she was curious to see what it was like down where I lived. I suspected it might have been that she didn’t want to be seen on a date with a woman up in her town, but wasn’t sure. She said she had found a babysitter, but only for a few hours, so our time would be tight. That worked perfectly with my schedule.
We met on a Saturday night at a tapas restaurant in town. Molly was attired in summer pastels, with a pair of chunky designer sunglasses pulling her long blond hair back, looking every bit a woman from Westport. She waved and smiled as we caught sight of each other, and exchanged pecks on the cheek. It being summertime in Westchester, the street traffic was light, so we had no problem securing a comfortable outdoor table.
Molly seemed totally at ease being out on a date with a woman—it was like two old friends catching up over a meal. We ordered a glass of wine and pulled out the menus, and over conversation discovered we had a fair amount in common, having both grown up in Jewish families in the Northeast. We played the Jewish geography of camp friends game, and actually knew some people in common. I was enjoying our dinner, but it had the feel of being out with a straight friend—which was also fine, just a fun night.
I knew she had to get back to the sitter, so after dinner I offered to pay the check and let her head out. She said of course not—let’s split it, and then without skipping a beat, winked at me and asked, Aren’t you going to show me where you live? I mean, she was a real estate agent! I wasn’t expecting Molly to be so forward, in fact she didn’t give off any gay vibe, but I reminded myself of my very imperfect gaydar, and so I just went with it.
She followed me back to my house, and in through the garage to the kitchen. Molly was definitely attractive, but I still felt unsure. I suspected, if anything, she was seeking an experimental first kiss with a woman to see what it was like. I poured us a glass of white wine as Molly explored my den. I mused, I’m sure you’ll want the real estate agent level tour, right? Almost without missing a beat, Molly flirtatiously smiled and quipped, No, just your bedroom.
Well, alright! That was unexpected.